JPS6129353B2 - - Google Patents
Info
- Publication number
- JPS6129353B2 JPS6129353B2 JP9640377A JP9640377A JPS6129353B2 JP S6129353 B2 JPS6129353 B2 JP S6129353B2 JP 9640377 A JP9640377 A JP 9640377A JP 9640377 A JP9640377 A JP 9640377A JP S6129353 B2 JPS6129353 B2 JP S6129353B2
- Authority
- JP
- Japan
- Prior art keywords
- dihydrocarbostyryl
- compound
- reaction
- general formula
- present
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OIALIKXMLIAOSN-UHFFFAOYSA-N 2-Propylpyridine Chemical compound CCCC1=CC=CC=N1 OIALIKXMLIAOSN-UHFFFAOYSA-N 0.000 description 1
- NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 description 1
- FRGXNJWEDDQLFH-UHFFFAOYSA-N 4-propan-2-ylpyridine Chemical compound CC(C)C1=CC=NC=C1 FRGXNJWEDDQLFH-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229960004676 antithrombotic agent Drugs 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
【発明の詳細な説明】
本発明は新規な３・４−ジヒドロカルボスチリ
ル誘導体に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel 3,4-dihydrocarbostyryl derivatives.
本発明の化合物は新規化合物であつて、一般式
〔式中Ｒは水素原子又は炭素数１〜３のアルキル
基を、Ｘはハロゲン原子を夫々示す。〕で表わさ
れる。該化合物は抗菌作用、消炎作用、血小板凝
集抑制作用を有し、抗菌剤、消炎剤、血栓予防薬
等として有用である。 The compound of the present invention is a new compound and has the general formula [In the formula, R represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and X represents a halogen atom. ]. The compound has antibacterial action, anti-inflammatory action, and platelet aggregation-inhibiting action, and is useful as an antibacterial agent, anti-inflammatory agent, antithrombotic agent, and the like.
上記一般式〔〕に於て、Ｒで示される炭素数
１〜３のアルキル基としては具体的にはメチル、
エチル、プロピル及びイソプロピル基である。ま
たＸで示されるハロゲン原子としては塩素原子、
臭素原子、沃素原子等を例示できる。 In the above general formula [], the alkyl group having 1 to 3 carbon atoms represented by R is specifically methyl,
Ethyl, propyl and isopropyl groups. In addition, the halogen atom represented by X is a chlorine atom,
Examples include bromine atom and iodine atom.
本発明の化合物は種々の方法にて製造される
が、その好ましい一例としては例えば下式に示す
如くして製造される。 The compound of the present invention can be produced by various methods, and a preferred example thereof is as shown in the following formula.
即ち一般式〔〕で表わされる公知の６−（３
−ハロゲノプロポキシ）−３・４−ジヒドロカル
ボスチリル誘導体、例えば６−（３−ブロモプロ
ポキシ）−３・４−ジヒドロカルボスチリル、６
−（３−クロロプロポキシ）−３・４−ジヒドロカ
ルボスチリル等と一般式〔〕で表わされる公知
のアミン、例えばピリジン、α−ピコリン、３−
エチルピリジン、２−プロピルピリジン、４−イ
ソプロピルピリジン等とを反応させることにより
本発明化合物が製造される。 That is, the well-known 6-(3
-halogenopropoxy)-3,4-dihydrocarbostyryl derivatives, such as 6-(3-bromopropoxy)-3,4-dihydrocarbostyryl, 6
-(3-chloropropoxy)-3,4-dihydrocarbostyryl, etc., and known amines represented by the general formula [], such as pyridine, α-picoline, 3-
The compound of the present invention is produced by reacting with ethylpyridine, 2-propylpyridine, 4-isopropylpyridine, etc.
本発明における上記反応は、無溶媒で或いは溶
媒中で行なわれる。ここで溶媒としては、反応に
関与しないものであればいずれも使用できる。代
表的溶媒を例示すれば、メタノール、エタノー
ル、プロパノール、イソプロパノール、ブタノー
ル、エチレングリコール等のアルコール類；ジメ
チルエーテル、テトラヒドロフラン、ジオキサン
等のエーテル類；アセトン、メチルエチルケト
ン、シクロヘキサノン、アセトフエノン等のケト
ン類；酢酸メチル、酢酸エチル等のエステル類；
Ｎ・Ｎ−ジメチルホルムアミド、ジメチルスルホ
キシド、ヘキサメチルリン酸トリアミド等の非プ
ロトン性極性溶媒；アセトニトリル等のニトリル
類等が挙げられる。一般式〔〕の化合物と一般
式〔〕の化合物との使用割合としては特に限定
されず広い範囲から適宜選択されるが、反応を無
溶媒下で行なう場合には通常前者に対して後者を
等モル〜太過剰量使用するのがよく、また反応を
溶媒中で行なう場合には通常前者に対して後者を
等モル〜５倍モル、好ましくは等モル〜２倍モル
量使用するのがよい。該反応は一般に０〜200
℃、好ましくは50〜150℃の温度下に良好に進行
し、通常10分〜10時間、長くとも24時間以内に完
結する。 The above reaction in the present invention is carried out without a solvent or in a solvent. Any solvent can be used as long as it does not participate in the reaction. Typical solvents include alcohols such as methanol, ethanol, propanol, isopropanol, butanol, and ethylene glycol; ethers such as dimethyl ether, tetrahydrofuran, and dioxane; ketones such as acetone, methyl ethyl ketone, cyclohexanone, and acetophenone; methyl acetate; Esters such as ethyl acetate;
Examples include aprotic polar solvents such as N.N-dimethylformamide, dimethylsulfoxide, and hexamethylphosphoric triamide; and nitriles such as acetonitrile. The ratio of the compound of general formula [] and the compound of general formula [] to be used is not particularly limited and is appropriately selected from a wide range, but when the reaction is carried out without a solvent, the latter is usually equal to the former. It is preferable to use a molar to large excess amount, and when the reaction is carried out in a solvent, the latter is usually used in an equimolar to 5-fold molar amount, preferably an equimolar to 2-fold molar amount, relative to the former. The reaction is generally between 0 and 200
The process progresses well at a temperature of 50 to 150°C, and is usually completed within 10 minutes to 10 hours, and at most 24 hours.
反応終了後は常法に従い例えば過濃縮、結晶
化、再結晶等の通常の分離手段により反応液から
目的物を分離精製すればよい。 After completion of the reaction, the target product may be separated and purified from the reaction solution by conventional separation means such as overconcentration, crystallization, recrystallization, etc. in accordance with conventional methods.
かくして本発明の３・４−ジヒドロカルボスチ
リル誘導体が収得できる。 In this way, the 3,4-dihydrocarbostyryl derivative of the present invention can be obtained.
本発明化合物の製造例を以下に掲げる。 Production examples of the compounds of the present invention are listed below.
製造例 １
６−（３−ブロモプロポキシ）−３・４−ジヒド
ロカルボスチリル1.0ｇにピリジン20mlを加えて
75〜80℃にて10分間撹拌する。析出してくる結晶
を取し、エーテルで洗浄し乾燥する。得られた
結晶をエタノールから再結晶して無色針状晶の６
−（３−ピリジニウムプロポキシ）−３・４−ジヒ
ドロカルボスチリルブロマイド0.85ｇを得る。Production example 1 Add 20 ml of pyridine to 1.0 g of 6-(3-bromopropoxy)-3,4-dihydrocarbostyryl.
Stir for 10 minutes at 75-80°C. Collect the precipitated crystals, wash with ether, and dry. The obtained crystals were recrystallized from ethanol to form colorless needle-like crystals.
0.85 g of -(3-pyridiniumpropoxy)-3,4-dihydrocarbostyryl bromide is obtained.
融点 190〜191.5℃
製造例 ２
６−（３−ブロモプロポキシ）−３・４−ジヒド
ロカルボスチリル1.0ｇにα−ピコリン４mlを加
えて90〜100℃にて３時間撹拌する。冷後析出晶
を取し、エーテルで洗浄し、エタノールから再
結晶して無色針状晶の６−（３−α−ピコリニウ
ムプロポキシ）−３・４−ジヒドロカルボスチリ
ルブロマイド1.3ｇを得る。Melting point 190-191.5°C Production example 2 4 ml of α-picoline was added to 1.0 g of 6-(3-bromopropoxy)-3,4-dihydrocarbostyryl and stirred at 90-100°C for 3 hours. After cooling, the precipitated crystals were collected, washed with ether, and recrystallized from ethanol to obtain 1.3 g of 6-(3-α-picolinium propoxy)-3,4-dihydrocarbostyryl bromide in the form of colorless needles.
融点 179〜181℃Melting point 179-181℃
Claims (1)
基を、Ｘはハロゲン原子を夫々示す。〕 で表わされる３・４−ジヒドロカルボスチリル誘
導体。[Claims] 1. General formula [In the formula, R represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and X represents a halogen atom. ] A 3,4-dihydrocarbostyryl derivative represented by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9640377A JPS5430180A (en) | 1977-08-10 | 1977-08-10 | 3,4-dihydrocarbostyril derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9640377A JPS5430180A (en) | 1977-08-10 | 1977-08-10 | 3,4-dihydrocarbostyril derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5430180A JPS5430180A (en) | 1979-03-06 |
| JPS6129353B2 true JPS6129353B2 (en) | 1986-07-05 |
Family
ID=14163986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9640377A Granted JPS5430180A (en) | 1977-08-10 | 1977-08-10 | 3,4-dihydrocarbostyril derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5430180A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0215861Y2 (en) * | 1984-12-22 | 1990-04-27 | ||
| DK167187A (en) | 1986-04-02 | 1987-10-03 | Otsuka Pharma Co Ltd | CARBOSTYRIC DERIVATIVES AND SALTS THEREOF, PROCEDURE FOR THE PREPARATION OF SUCH COMPOUNDS AND MEDICINAL CONTAINING THESE |
| JPH0440039U (en) * | 1990-06-02 | 1992-04-06 |
-
1977
- 1977-08-10 JP JP9640377A patent/JPS5430180A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5430180A (en) | 1979-03-06 |
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